Two-Week Italy Self-Drive Road Trip With Itinerary from Milan to Como, Verona, Venice, Florence, Siena, and Rome

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Photo of Arch of Peace, or Arco della Pace, city gate in the centre of the Old Town of Milan in the sunny day, Lombardia, Italy.
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Explore the best of Italy on a remarkable 15-day road trip! Combine exploration with relaxation on a self-drive tour featuring Milan, Como, Lenno, Colonno, Verona, Venice, Florence, Pisa, Siena, Rome, and Bologna.

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 3 nights in Milan, 1 night in Como, 1 night in Verona, 2 nights in Venice, 3 nights in Florence, 1 night in Siena, and 3 nights in Rome. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have you covered.

Upon arriving in Milan, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery.

As you hit the open road and drive through Milan, Como, Lenno, Colonno, Verona, Venice, Florence, Pisa, Siena, Rome, and Bologna, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodations, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!

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Driver’s age is 30 - 65
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Pick-up: 10:00
Drop-off: 10:00

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Day 1

Day 1

  • Milan - Arrival day
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  • Pinacoteca di Brera
  • More

Say hello to Milan! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Milan for 2 nights before you continue your adventure!

Milan is a beautiful city with plenty to discover. Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Milan. Make yourself at home and unwind before heading out again.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Milan, it's often a good idea to reserve a table in advance.

Raise a toast to the start of your 15-day road trip in Italy!

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Day 2

Day 2

  • Milan
  • More

Drive 8 km, 51 min

  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • Castello Sforzesco
  • Sempione Park
  • Piazza Gae Aulenti
  • Navigli
  • More

You have 1 night left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Milan.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

Bring home unique finds from Milan's bustling shopping hub, Quadrilatero della Moda. Enjoy a leisurely exploration of unique boutiques and high-end stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Quadrilatero della Moda offers plenty of options, including primary services, unique landmarks, and community events.

After a day of adventure, treat yourself to an exquisite dinner at one of Milan's best restaurants.

Savor another day of unforgettable experiences in Italy!

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Day 3

Day 3

  • Milan
  • Como
  • More

Drive 117 km, 2 hours 47 min

  • Basilica di San Fedele
  • Cattedrale di Santa Maria Assunta - Duomo di Como
  • Villa Carlotta
  • Villa del Balbianello
  • Greenway del Lago di Como
  • More

Your itinerary for day 3 of your road trip in Italy includes 4 stops and features some of the highlights of Como, Rogaro, Lenno, and Colonno. At the end of the day, enjoy the comforts of a top-rated hotel in Como, where you'll spend 1 night.

When you’re done exploring for the day, you’ll drive to your hotel in Como. Check in and relax before you head out to tour the city.

Como is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Como.

Celebrate another amazing day of your road trip adventure in Italy!

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Day 4

Day 4

  • Como
  • Verona
  • More

Drive 203 km, 3 hours 6 min

  • Giusti Garden
  • Ponte Pietra
  • piazza dei Signori
  • piazza delle Erbe
  • Castelvecchio Museum
  • Verona Arena
  • More

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Verona. When you’re not sightseeing, take time to relax at your chosen hotel in Verona, where you’ll be staying for 1 night.

At the end of the day, you will drive to Verona, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Verona. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Relax and look forward to more memorable moments to come!

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Day 5

Day 5

  • Verona
  • Venice
  • More

Drive 127 km, 2 hours 29 min

  • Santa Maria della Salute
  • Peggy Guggenheim Collection
  • Basilica S.Maria Gloriosa dei Frari
  • Grand Canal
  • More

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Venice. At the end of the day, you will retreat to the hotel of your choice in Venice, where will spend 2 nights.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Venice. Venice offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

Indulge in a memorable dining experience at one of Venice's most popular restaurants, and connect with friendly locals for a true cultural experience.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

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Day 6

Day 6

  • Venice
  • More

Drive 2 km, 36 min

  • Rialto Bridge
  • Teatro La Fenice
  • Piazza San Marco
  • St Mark's Basilica
  • Doge's Palace
  • Bridge of Sighs
  • More

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Venice. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Head back to your accommodation in Venice and get some rest to prepare for another magical day of your road trip in Italy.

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Day 7

Day 7

  • Venice
  • Florence
  • More

Drive 264 km, 3 hours 52 min

  • piazzale Michelangelo
  • Basilica of Santa Croce in Florence
  • David
  • Central Market
  • Cathedral of Santa Maria del Fiore
  • More

Dive into day 7 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Florence. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 3 nights.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax before you head out to tour the city.

After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.

Relax and recharge in preparation for another adventurous day in Italy!

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Day 8

Day 8

  • Florence
  • More

Drive 1 km, 23 min

  • Ponte Vecchio
  • piazza della Signoria
  • Bargello National Museum
  • Palazzo Vecchio
  • Uffizi Gallery
  • Oltrarno
  • More

You’ll stay in Florence for 2 nights.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

Raise your glass and celebrate another amazing day of your road trip in Italy!

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Day 9

Day 9

  • Florence
  • More

Drive 176 km, 3 hours 7 min

  • Santa Maria della Spina
  • Knights' Square
  • Leaning Tower of Pisa
  • Pisa Cathedral
  • Piazza del Duomo, Pisa
  • Campo santo
  • More

On day 9 of your road trip, you'll get the chance to experience Pisa. At the end of the day, you'll drive back to Florence, where you still have 1 night left to stay.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Florence, it's often a good idea to reserve a table in advance.

Celebrate another amazing day of your road trip adventure in Italy!

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Day 10

Day 10

  • Florence
  • Siena
  • More

Drive 84 km, 1 hour 58 min

  • Porta Romana
  • Palazzo Salimbeni
  • Basilica of San Domenico
  • Siena Cathedral
  • Pubblico Palace
  • piazza del Campo
  • More

On day 10 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Siena are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Throughout the day, make sure to take breaks to appreciate the surroundings.

At the end of the day, you will drive to Siena, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine.

Get a good night's sleep and look forward to another great day on the road in Italy!

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Day 11

Day 11

  • Siena
  • Rome
  • More

Drive 248 km, 3 hours 21 min

  • Colosseum
  • Roman Forum
  • piazza del Popolo
  • Capitoline Museums
  • More

Your itinerary for day 11 of your road trip in Italy includes 1 stop and features some of the highlights of Rome. At the end of the day, enjoy the comforts of a top-rated hotel in Rome, where you'll spend 3 nights.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Rome. Rome offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Rome, it's often a good idea to reserve a table in advance.

Say good night to Rome and look forward to another great day of your road trip in Italy!

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Day 12

Day 12

  • Rome
  • More

Drive 8 km, 57 min

  • Vatican Museums
  • Sistine Chapel
  • St Peter's Basilica
  • Campo de' Fiori
  • Piazza Navona
  • Trastevere
  • More

Greet day 12 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 2 nights to stay in Rome, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Vatican City and Rome.

Set aside time today to explore Trastevere, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Rome.

After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.

Say good night to Rome and look forward to another great day of your road trip in Italy!

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Day 13

Day 13

  • Rome
  • More

Drive 13 km, 1 hour 27 min

  • St. Clement Basilica
  • Spanish Steps
  • Piazza di Spagna
  • Trevi Fountain
  • Pantheon
  • Castel Sant'Angelo
  • More

Day 13 offers an itinerary packed with the best things to see in Milan. You’ll stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Throughout the day, make sure to take breaks to appreciate the surroundings.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

Indulge in a memorable dining experience at one of Rome's most popular restaurants, and connect with friendly locals for a true cultural experience.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

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Day 14

Day 14

  • Rome
  • Milan
  • More

Drive 602 km, 7 hours 8 min

  • Bologna Cathedral
  • Piazza Maggiore
  • Two Towers
  • Porta Maggiore
  • More

On day 14 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Bologna. When you’re not sightseeing, take time to relax at your chosen hotel in Milan, where you’ll be staying for 1 night.

When you’re done exploring for the day, you’ll drive to your hotel in Milan. Check in and relax before you head out to tour the city.

Milan is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Milan.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

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Day 15

Day 15

  • Milan - Departure day
  • More
  • Via Monte Napoleone
  • More

Day 15 of your road trip in Italy is your departure day. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

If you’re in the mood for luxury shopping, high-end stores await you.

Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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Your trip is protected, personalized, and priced right. No surprises, no stress.

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